Keeping cygwin updated on remote systems

[DePriest, Jason R.]

I have about 20 systems that are either behind firewalls that I don't
control or hardened so that my only access to them is via SSH.

I am using OpenSSH installed with the Cygwin setup.exe program and
configured with the included scripts.

I also tunnel VNC through SSH to get a remote desktop when necessary.

My problem is: how do I keep these systems updated since my only
access is through the components I need to update?

I am also trying to find a way to avoid manually connecting to each
system to run setup.exe and then rebooting it so in-use files can be
updated.

Does anyone have any methods they use to handle this?

The 20 systems should all be mostly identical.  So my first thought
was to create a representative build in a test lab, keep it updated,
and then batch an rsync over SSH of the files to the 20 systems
identically up-to-date.

How can I handle in-use files if I am not using setup.exe?

I would love to hear any suggestions that anyone has.

-Jason

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